Simply Sailing Private Sail from Sapphire Marina

The best thing about this trip is its simple plan: board at Sapphire Beach, point the bow toward the waters around St. Thomas and St. John, and spend three hours sailing without a packed schedule. Captain Rob and Captain Deb run the boat, and the private setup means your group of up to six has the whole outing to itself.

I like the easy dock boarding and the fact that drinks, snacks, water, and alcohol are already covered. I also like the choice of a morning or afternoon start, which makes it easier to fit sailing around a beach day or other plans. The main consideration is that this is primarily a sailing trip, not an island-hopping tour. There are no planned stops unless you request a snorkel break.

Key points to know before booking

• Pure sailing around St. Thomas and St. John: The planned experience keeps you on the water rather than moving from stop to stop.
• Private boat for up to six people: The $799 price covers the group, not each person individually.
• A 40-foot pilothouse mariner: You get a proper sailing vessel with easy boarding at the dock.
• Morning or afternoon departures: Choose the time that fits your day and your preferred light on the water.
• Snorkeling is optional: Ask for a snorkel stop if that matters to your group, since it is not part of the basic no-stop plan.
• Plan for a 20 percent crew gratuity: The tip is not included in the listed price.

Setting out from Sapphire Beach

Your meeting point is Sapphire Beach in Smith Bay, on the east side of St. Thomas. The boat returns to the same place at the end, so you do not need to arrange a second pickup point or figure out how to get back from another harbor.

Boarding is described as easy, with access directly at the dock. That matters more than it may sound. A private charter works best when the start is calm and direct, without a long transfer or a complicated marina routine. Confirmation arrives at booking, and the meeting area is near public transportation.

The boat is a 40-foot pilothouse mariner. That gives you a proper sailing platform rather than a quick ride in a small open boat. The supplied details do not specify the exact seating arrangement, cabin facilities, or shade setup, so ask the operator if those points matter to your group.

Once everyone is aboard, the outing settles into its main rhythm: sailing. There is no long sightseeing lecture or list of scheduled stops to keep up with. You are there to watch the islands shift around you, feel the boat move under sail, and enjoy a quiet stretch on the water.

Three hours between St. Thomas and St. John

The route takes you through the waters of St. Thomas and beautiful St. John. The details do not promise a fixed route, specific beaches, or a guaranteed view of any particular landmark. That is useful to understand before you book, since the appeal comes from the time spent sailing rather than from checking off named locations.

The trip lasts about three hours. That is long enough to feel like a real outing, but short enough to fit into a morning or afternoon without taking over your whole day. If you are staying in St. Thomas for only a few days, this length gives you a clear block of time on the water while leaving room for other plans.

The boat may spend much of the trip underway. You can expect the scenery to come from the islands, the water, and the changing position of the boat. Sailing gives you a different view than a beach visit or a land-based drive. You see the shoreline from offshore and get a sense of how St. Thomas and St. John sit in relation to one another.

Still, keep the promise of the experience in mind. This is not presented as a narrated island tour, a lunch cruise, or a beach-hopping charter. If you want several landings, a long swim, or a string of photo stops, you may find the plan too spare. If you like the idea of letting the boat do the work while you enjoy the ride, the plain approach is the point.

A flexible snorkel option

The standard plan is no stops and pure sailing. You can request a snorkel stop, which gives your group some control over the shape of the afternoon. The information provided does not name a particular reef, beach, or snorkeling site, and it does not say whether gear is included.

That means you should ask about the snorkel details before departure if swimming is important to you. Confirm whether equipment is supplied, how much time can be spent in the water, and how the stop might affect the sailing route.

This option is most useful for groups with mixed interests. One person may want a calm sail, while another hopes to get in the water. The private format lets you discuss that preference with the captains instead of following a fixed group schedule. Still, do not assume the snorkel stop happens automatically. Request it when booking or before setting out.

If your top goal is snorkeling, compare this charter with a trip designed specifically around reefs and swim time. If you want sailing first, with the option to add a short water stop, this arrangement gives you more room to shape the outing.

Captain Rob, Captain Deb, and the feel onboard

Captain Rob and Captain Deb are named as the operators of the charter. Their role matters because a private sailing trip depends heavily on the people running the boat. The personal feel is part of the experience, especially when your group is small and the outing is built around time together rather than a set list of attractions.

The tone appears warm and welcoming. A family described being greeted with warmth and enthusiasm, and another group praised the hosts after a pleasant afternoon sail. Those details point to an experience that is friendly rather than formal.

You should still think about what kind of guidance you want. The supplied information does not promise a detailed lesson in sailing, a narrated tour, or a formal educational program. You may get conversation and local direction from Rob and Deb, but the central activity remains simply sailing.

That can be a real advantage. You are not pushed from one activity to another, and you do not have to make small talk with a boatload of strangers. For a family, couple, or group of friends who want private time together, this is an easygoing setup.

Snacks and drinks included in the $799 price

The charter costs $799 per group of up to six people. At full capacity, that works out to about $133 per person before gratuity. A customary 20 percent crew tip would add $159.80 to the group bill, bringing the total to about $958.80, or roughly $159.80 per person if six people share the cost.

That is the right way to judge this price. For two people, the per-person cost is high. For six, the private format becomes much more competitive, especially because you are not paying separate admission fees for each person and you have the boat to yourselves.

The package includes soda, bottled water, alcoholic beverages, and snacks. Those inclusions simplify the outing. You do not need to pack a cooler or plan a meal around the three-hour schedule. The details do not specify the brands, amount, or selection, so bring any special drinks or food needs only after checking what the operator can accommodate.

Alcohol is included, but use common sense on a moving boat. The value here is not simply the free drinks. It is the convenience of having refreshments on hand while your group settles into the sail.

The gratuity is separate and customary at 20 percent. Build that into your budget from the start rather than treating it as an unexpected extra. Also remember that transport to Sapphire Beach is not listed as part of the charter price.

Morning or afternoon: choosing your sailing time

You can choose a morning or afternoon departure. That flexibility is helpful in St. Thomas, where a sailing trip may need to share the day with beach time, shopping, meals, or other bookings.

A morning trip may suit you if you want to spend the rest of the day on land. An afternoon start may work better if you prefer a slower beginning or want your time on the water to be the main event later in the day. The supplied details do not promise sunset sailing, so do not book it expecting a dedicated sunset cruise.

Think about your group before choosing. Families may prefer the time that fits naps, meals, or a quieter start. Couples and friends may simply choose the slot that leaves the rest of the day open. Since the trip lasts about three hours and returns to Sapphire Beach, the timing is easy to understand.

The weather matters. Sailing depends on suitable conditions, and poor weather can lead to a new date or a full refund. That policy is reassuring, but it also means you should avoid planning an important same-day connection around this trip.

Who gets the most from this private charter

This charter fits you best if you value privacy, a small group, and time on the water more than a busy itinerary. Six friends sharing the boat can split the cost and enjoy a private setting without strangers joining the trip.

It also suits families who want a manageable three-hour outing. Most people can participate, and the dock boarding is described as easy. Still, the operator does not provide detailed information about mobility equipment, steps, restrooms, or shade, so ask specific questions if anyone in your group has access needs.

Couples can book it too, but the price is harder to justify with only two people. The private boat and included refreshments may still be worth it for a special occasion, but the value improves sharply as your group gets closer to six.

Sailing fans will appreciate the focus. You are not being promised a crowded party boat or a rushed list of attractions. On the other hand, if your group wants loud entertainment, extensive narration, or multiple beach stops, this will likely feel too quiet and too simple.

The trip is also a good match for anyone who has already seen St. Thomas from land and wants a different view. The water changes the scale of the islands. Instead of looking out from a beach, you watch the coast from the moving deck and spend the full outing in the island setting.

Booking details, weather, and cancellation

This is a private activity, so only your group participates. The price covers up to six people, and the activity ends back at Sapphire Beach.

You receive confirmation when booking, and mobile tickets are accepted. The charter is often reserved well ahead of time, with bookings averaging 26 days in advance, so it is sensible to arrange it early if your dates are fixed.

You can cancel for a full refund up to 24 hours before the local start time. Changes or cancellations inside that 24-hour window are not accepted for a refund. If poor weather causes the operator to cancel, you can choose a different date or receive a full refund.

That weather provision is important for a sailing trip. Keep your schedule flexible enough to handle a change, and avoid placing this outing immediately before a flight or another nonrefundable activity.

Is Simply Sailing worth booking?

Book this charter if you want a private, unhurried three hours around St. Thomas and St. John, especially if you have four to six people to share the $799 cost. The included drinks and snacks, easy boarding, and optional snorkel stop make the plan practical without making it busy.

Skip it if you mainly want snorkeling, beach landings, or a narrated sightseeing route. The strongest reason to book is the sailing itself, with Rob and Deb at the helm and your own group on a 40-foot boat. Ask about the snorkel setup, onboard facilities, and refreshments before you go, then budget the 20 percent crew gratuity. For the right group, this is a relaxed way to see the Virgin Islands from the water without turning the day into a production.

FAQ

Where does the sailing trip start and end?

It starts at Sapphire Beach in Smith Bay, St. Thomas, and returns to the same meeting point at the end.

How long does the charter last?

The sailing lasts approximately three hours.

How many people can join the private charter?

The $799 group price covers up to six people. Only your group participates.

What is included in the price?

Soda, bottled water, alcoholic beverages, snacks, and easy boarding access at the dock are included.

Can I choose a morning or afternoon departure?

Yes. You can choose between a morning or afternoon departure.

Is snorkeling included?

A snorkel stop can be added if requested. The standard plan is pure sailing with no stops.

What happens if the weather is poor?

If the trip is canceled because of poor weather, you can choose a different date or receive a full refund. You can also cancel for a full refund up to 24 hours before the local start time.